Hydrochloric Acid → HCID 66774305, compound

HRID 255168Notes

Reaction equation

HRID 255168 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[CH:19]=[C:18]2[C:28]([O:30][CH3:31])=[O:29])[CH2:11][CH2:10]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[CH:19]=[C:18]2[C:28]([O:30][CH3:31])=[O:29])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66774230HCID 66774230, compound2×

Product 1

HCID 66774305HCID 66774305, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of methyl 1-(2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl)-6-methoxy-1H-indole-2-carboxylate (Intermediate 13, 520 mg, 1.2 mmol) in dioxane (4 mL) was treated at room temperature under vigorous stirring with a solution of HCl in dioxane (4M, 2 mL). After 3 days, the reaction mixture was concentrated under reduced pressure. The residue was taken up in dichloromethane (60 mL) and saturated aqueous sodium hydrogen carbonate solution (10 mL), the aqueous phase was extracted three times with dichloromethane (3×50 mL) and the combined organic phases were dried over sodium sulfate to give 407 mg (100% yield) of the crude product as colorless solid, mp 101° C.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionsaturated aqueous sodium hydrogen carbonate solution (10 mL), the aqueous phase was extracted three times with dichloromethane (3×50 mL)
  3. dry with materialthe combined organic phases were dried over sodium sulfate

Sources & evidence

ORD record
ord-b8814f4945cd4ea7961a8ba5a2cf750d
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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